Windows 10 Extended Security Issues?

[DrZoidberg]

I am still unable to get Windows to install Win10 extended security updates. It has enroll button, but basically freezes that self closes empty dialog box and nothing happens. Nearly March. That's 5 months without support. Anyone else still having issues? Last few times I contacted Microsoft they just say it's being rolled out in stages and it might not be available to me for months.

 

[RianKellyIT]

To be fair, had this exact issue with a few client machines last year. The ESU enrollment dialog freezing and closing is usually one of two things.
First, make sure you've got the latest servicing stack update (SSU) installed before trying to enroll, Microsoft won't always tell you that's the blocker but it is.
Second, there's a known issue where the enrollment fails silently if your Windows activation isn't fully verified, even if it shows as activated. Try running slmgr /dlv in an elevated command prompt and check the license status is properly licensed, not just "notification mode."
If that all looks fine, the other thing I've seen work is manually downloading the ESU preparation package (KB5015684) from the Microsoft Update Catalog and installing it directly before trying the enrollment again. Some machines just don't pick it up through Windows Update properly.
One more thing worth checking, if you're on a domain or have any group policies applied, there's a policy under Computer Configuration > Administrative Templates > Windows Components > Windows Update that can interfere with ESU enrollment. Worth having a look if none of the above sorts it.
Let us know how you get on with those steps.

 

[RianKellyIT]

Had this exact scenario on a couple of client machines. The advice about SSU and slmgr /dlv is spot on, worth checking those first.

One thing not mentioned yet: before you try enrolling again, make sure KB5048456 (the ESU Preparation Package for Windows 10) is installed. Microsoft made this a prerequisite but does not always surface it in Windows Update automatically. You can grab it directly from the Microsoft Update Catalog by searching KB5048456 along with your Windows 10 version and architecture.

After installing that, run gpupdate /force from an elevated command prompt before trying the enrollment dialog again.

Also worth confirming: the free ESU option is only available to devices that are genuinely activated with a retail or OEM license. Volume License customers and Microsoft 365 subscribers get it included. If your machine is activated through KMS or MAK on a corporate volume license, the enrollment process is slightly different and goes through the Volume Licensing Service Center.

If all else fails and Microsoft support keeps saying "being rolled out in stages", that is often code for an underlying activation or license type issue that their front-line support will not diagnose without escalation. Worth asking them specifically to check your device's eligibility status in their backend, not just the general rollout timeline.